Electronic devices, such as portable electronic devices, mobile devices, and so forth, typically include operating software such as firmware, operating systems, etc. This operating software may be updated from time to time. For example, an updated operating system (e.g., a software image of an operating system) may be retrieved from a server and installed on an electronic device replacing a previous version of the operating system. In some instances, the electronic device may be communicatively coupled with another computing device to perform updates to the operating software. For example, a portable electronic device may be communicatively coupled to a personal computer using a universal serial bus cable that facilitates control of the portable electronic device by the personal computer. In such an example, the personal computer may retrieve the operating software, transfer the operating software to the portable electronic device, cause the operating software to be installed on the portable electronic device, and cause the operating system to reboot. In some instances, the personal computer may also cause updated applications to be installed on the portable electronic device. For example, following the reboot, the personal computer may transfer one or more applications to the portable electronic device, cause the one or more applications to be installed, and cause the portable electronic device to be rebooted a second time.